Here are 1-3 brief analogies for Tiptree (TIPT):

• A mini-Berkshire Hathaway, but specifically focused on financial services and specialty insurance.
• A diversified financial services company, similar to how Apollo Global Management operates its Athene insurance arm alongside other investment businesses.

• Specialty Insurance: Providing a range of property, casualty, warranty, and surety insurance products through its Fortegra subsidiary.
• Asset Management: Managing a diversified investment portfolio across various asset classes, including real estate and credit.

Tiptree (TIPT) operates primarily as a financial services holding company. Its main operating businesses, Fortress Investment Group (investment management) and its InsurTech segments, primarily serve institutional clients and other businesses (B2B).

Due to the highly diversified nature of its client base in investment management and insurance, and standard industry practices regarding client confidentiality, Tiptree does not publicly disclose specific "major customer companies" that account for a significant portion of its revenues. Therefore, it is not possible to list named major customer companies with their stock symbols.

However, Tiptree's subsidiaries serve a broad range of clients, primarily including various categories of:

• Institutional Investors: This includes entities such as public and corporate pension funds, sovereign wealth funds, university endowments, and charitable foundations that invest in Fortress's various funds.
• Insurance Intermediaries and Partners: Businesses like program administrators and wholesale brokers through whom its InsurTech segment writes specialized property and casualty insurance. These intermediaries connect Tiptree's insurance products to ultimate policyholders, which can be individuals or other businesses.

While Fortress also serves high-net-worth individuals, the primary customer base for Tiptree's core operations consists of the aforementioned institutional and business clients. No individual client typically represents a material portion of Tiptree's consolidated revenues.

• Hannover Re (HNRGY)
• Everest Re Group, Ltd. (ER)
• Munich Re (MURGY)
• PartnerRe Ltd.

Jonathan Ilany, Chief Executive Officer & Director

Jonathan Ilany was appointed CEO in February 2015, having served as Co-Chief Executive Officer and Executive Vice President, Head of Mortgage Finance and Asset Management since October 2014. Prior to Tiptree, he was a partner at Mariner Investment Group from 2000 to 2005 and continued as a passive partner since 2005. He also previously held roles at Bear Stearns and Merrill Lynch. He served as the Chief Executive Officer of Angiosonics, Inc.

Scott McKinney, Chief Financial Officer

Scott McKinney assumed the role of Chief Financial Officer in March 2023. Before this, he served as Deputy Chief Financial Officer from April 2022 and as Director of Financial Planning and Analysis, where he oversaw strategic planning, financial analysis, and investor relations. Mr. McKinney joined Tiptree in February 2016 from General Electric Company, where he held various finance executive positions.

Michael G. Barnes, Executive Chairman of the Board

Michael G. Barnes has served as the Chairman of Tiptree since its inception in 2007. He is a founding partner of Tricadia Holdings, LP, a privately held company that provides investment management services. Before co-founding Tricadia in 2003, Mr. Barnes was responsible for overseeing various credit trading strategies at UBS, PaineWebber, and Bear Stearns.

Randy Maultsby, President and Head of Corporate Strategy & Development

Randy Maultsby became President in July 2021 and is also a member of the Board of Directors. He previously served as a Managing Director of Tiptree since 2010. In his role as President, Mr. Maultsby focuses on corporate strategy and development, including the company's acquisition, disposition, and capital markets activities. Before joining Tiptree, he was a Senior Vice President in the investment banking division of Fox-Pitt, Kelton, providing strategic advice to clients in banking, finance, asset management, and brokerage. His career also includes positions at JP Morgan, Conning & Company, and Citigroup.

Neil Rifkind, Vice President, General Counsel & Secretary

Neil Rifkind has held the position of Vice President, General Counsel and Secretary since July 2013. Prior to joining Tiptree, he was Special Counsel at Schulte Roth & Zabel LLP from 2011 to 2013, focusing on mergers and acquisitions and securities law. He also worked as an associate at Schulte Roth & Zabel LLP from 2006 to 2010 and at Fried, Frank, Harris, Shriver & Jacobson LLP from 1998 to 2006.

• The accelerating shift towards home-based care and advanced telehealth technologies, which could significantly diminish the long-term demand for traditional senior living and skilled nursing facilities, impacting Tiptree's healthcare real estate investments through Invesque.
• The rapid global push for decarbonization and the mandated transition to alternative fuels and propulsion technologies within the shipping industry, which could render Tiptree's existing fossil-fuel-dependent shipping assets technologically obsolete or subject to prohibitive operating costs due to new environmental regulations.

Tiptree Inc. (TIPT) operates primarily in three main segments: Specialty Insurance, Mortgage Origination and Servicing, and Asset Management. The addressable markets for these services are as follows:

Specialty Insurance

• The global specialty insurance market was valued at approximately $104.7 billion in 2021 and is projected to reach $279 billion by 2031, growing at a Compound Annual Growth Rate (CAGR) of 10.6% during this period.
• Another estimate places the global specialty insurance market size at USD 101.15 billion in 2024, with a projection to increase to USD 266.15 billion by 2032, exhibiting a CAGR of 13.1%.
• North America held a dominant share of the specialty insurance market, valued at USD 34.63 billion in 2023 and USD 38.86 billion in 2024.
• The U.S. market specifically is estimated to reach USD 29.15 billion in 2025.

Mortgage Origination and Servicing

• The U.S. home loan market reached approximately USD 2.29 trillion in 2025 and is forecasted to grow to USD 3.02 trillion by 2030, with a CAGR of 5.63%.
• U.S. mortgage originations totaled $1.69 trillion in 2024.
• Americans originated $884 billion in new mortgage debt in the first half of 2025.
• The U.S. mortgage lending market is projected to maintain a CAGR exceeding 5% from 2025 to 2033.

Asset Management

• The global asset management industry, in terms of assets under management (AuM), grew to a record-breaking $128 trillion in 2024.
• The global asset management market, which includes asset management solutions and services, was valued at USD 458.02 billion in 2023 and is expected to reach USD 571.77 billion in 2024. This market is projected to grow at a CAGR of 36.4% from 2024 to 2030, reaching USD 3,677.39 billion by 2030.
• North America dominated the asset management market with a revenue share of 33.59% in 2024. The U.S. asset management market size was exhibited at USD 189.07 billion in 2024 and is projected to be worth around USD 3,697.19 billion by 2034.

Tiptree (TIPT) is expected to drive future revenue growth over the next 2-3 years through several key areas, primarily centered around its specialty insurance operations and strategic capital allocation post-divestitures.

1. Continued Expansion in Specialty Insurance Lines: Tiptree's subsidiary, Fortegra, has been a significant driver of revenue growth, fueled by the expansion of its specialty insurance lines, particularly in the excess and surplus (E&S) market. This includes consistent growth in overall premiums and increased retention across both E&S and admitted property & casualty (P&C) lines. Fortegra's strong underwriting performance and ability to scale profitably within the specialty insurance space are highlighted as key strengths.
2. European Market Expansion: Fortegra has actively expanded its presence in Europe, as evidenced by acquisitions such as ITC Compliance in April 2022 and Premia in February 2023. These strategic moves are aimed at further broadening its European footprint.
3. Enhanced Investment Portfolio Performance: Increased net investment income and investment gains have contributed to Tiptree's overall revenue. The company has taken a more aggressive stance with its investment portfolio, including a higher allocation to BBB exposure and lower cash and cash equivalents, which is expected to benefit from potential rate cuts and generate strong book yields. Growing investable assets and maturing positions are also contributing to a steady improvement in book yield.
4. Strategic Deployment of Capital from Divestitures: Tiptree has agreed to sell Fortegra for $1.65 billion and its mortgage business, Reliance First Capital, for $51 million, with both transactions anticipated to close in 2026. The proceeds from these sales will be strategically deployed to create long-term value, focusing on strategic investments, opportunistic share buybacks, and thoughtful consideration of dividends. This capital allocation strategy aims to support future growth by investing in select small and middle-market companies across diverse industries, particularly within the insurance and credit-related financial sectors.

Share Repurchases

• Tiptree's Board of Directors authorized a share repurchase program of up to $20 million.
• As of December 31, 2024, approximately $11.945 million remained authorized for future share repurchases.
• No shares were repurchased during the year ended December 31, 2024.

Share Issuance

• In 2022, warrants were exercised for 1,999,989 shares of Tiptree common stock, resulting in $13.724 million in cash proceeds for 1,979,325 of those shares.
• The company's shares outstanding have shown a general increase from 33.21 million in 2020 to 37.49 million as of November 2025.

Inbound Investments

• In October 2021, private-equity firm Warburg Pincus made a $200 million strategic investment in Tiptree's Fortegra insurance business, acquiring approximately 24% ownership.
• This investment by Warburg Pincus also included 7-year warrants that, if exercised, could lead to Warburg owning an additional 3.8% of Fortegra.
• In 2024, Tiptree, Warburg, and Fortegra directors collectively contributed an aggregate capital of $40 million to Fortegra's total stockholders' equity.

Outbound Investments

• In September 2025, Tiptree agreed to sell its Fortegra insurance business for $1.65 billion, with an estimated $1.12 billion in gross proceeds to Tiptree, with the transaction anticipated to close in mid-2026.
• In October 2025, the company agreed to sell its mortgage business, Reliance First Capital, for an estimated $51 million, with closing expected in the first quarter of 2026.
• In 2022, Tiptree monetized its investments in the marine shipping sector through the sale of vessels for a total of $117 million, generating a net gain of approximately $35 million.

Capital Expenditures

• Tiptree has projected capital expenditures of $12 million for 2025, $12 million for 2026, and $12 million for 2027.